WO2010055122A1 - Octenidin-zusammensetzung - Google Patents

Octenidin-zusammensetzung Download PDF

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Publication number
WO2010055122A1
WO2010055122A1 PCT/EP2009/065111 EP2009065111W WO2010055122A1 WO 2010055122 A1 WO2010055122 A1 WO 2010055122A1 EP 2009065111 W EP2009065111 W EP 2009065111W WO 2010055122 A1 WO2010055122 A1 WO 2010055122A1
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WO
WIPO (PCT)
Prior art keywords
octenidine
kit
solution
polyhydric alcohol
polyalcohol
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PCT/EP2009/065111
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German (de)
English (en)
French (fr)
Inventor
Ahmet Melih Aydinoglu
Original Assignee
Ahmet Melih Aydinoglu
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40383579&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2010055122(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to AU2009315654A priority Critical patent/AU2009315654B2/en
Priority to CN2009801448968A priority patent/CN102209542A/zh
Priority to BRPI0915269A priority patent/BRPI0915269A2/pt
Priority to SI200930217T priority patent/SI2291185T1/sl
Priority to UAA201107410A priority patent/UA108190C2/ru
Priority to EP09756292A priority patent/EP2291185B1/de
Priority to DK09756292T priority patent/DK2291185T3/da
Priority to MX2011005092A priority patent/MX2011005092A/es
Priority to US13/128,266 priority patent/US8940324B2/en
Priority to ES09756292T priority patent/ES2381815T3/es
Priority to PL09756292T priority patent/PL2291185T3/pl
Priority to JP2011536025A priority patent/JP5756018B2/ja
Priority to RSP20120133 priority patent/RS52299B/en
Priority to CA2742921A priority patent/CA2742921A1/en
Priority to AT09756292T priority patent/ATE538788T1/de
Priority to EA201100762A priority patent/EA028177B1/ru
Priority to NZ59277509A priority patent/NZ592775A/en
Application filed by Ahmet Melih Aydinoglu filed Critical Ahmet Melih Aydinoglu
Publication of WO2010055122A1 publication Critical patent/WO2010055122A1/de
Priority to ZA2011/03126A priority patent/ZA201103126B/en
Priority to IL212596A priority patent/IL212596A/en
Priority to HK11107685A priority patent/HK1156838A1/xx
Priority to HRP20120277AT priority patent/HRP20120277T1/hr
Priority to US14/528,869 priority patent/US20150126557A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations

Definitions

  • the present invention relates to the field of disinfecting and antiseptic formulations and their applications.
  • Octenidine dihydrochloride is a microbiocidal active substance which is mainly used in skin, mucous membrane and wound antiseptics.
  • the marketing takes place under the trade name Octenisept ® . Due to its broad spectrum of activity on the one hand and good tolerability on the other hand, this active ingredient is becoming increasingly important in the practice of antiseptics and has already replaced classical antiseptic agents such as chlorhexidine, triclosan and PVP-iodine in some indication areas.
  • Octenidine or octenidine dihydrochloride and its derivatives are described in US patents US 4,206,215 and US 4,442,125 as anti-microbial substance.
  • DE 3 925 540 C1 relates to an aqueous antiseptic composition
  • an aqueous antiseptic composition comprising octenidine and phenoxyethanol and / or phenoxypropanol, which are used as solubilizers.
  • DE 10 2004 052 308 A1 and WO 2006/039961 relate to lozenges comprising octenidine, which is provided in a solid matrix of sugar.
  • This matrix is a solid mass of sugar in the range of 70-99.95% by weight, which serves as a carrier and covers the bitter taste of octenidine.
  • WO 2007/023066 A1 relates to a solution of octenidine dihydrochloride and a mono- or dihydric alcohol or glycerol. These alcohols are used as an alternative to conventional phenoxyethanol or phenoxypropanol from earlier octenidine dihydrochloride preparations.
  • WO 2007/031519 A2 relates to octenidine dihydrochloride preparations in the form of enveloping liposomes.
  • the use of phospholipid liposomes aims to reduce the cytotoxicity of octenidine.
  • EP 1 683 416 A relates to the addition of alcohol to octenidine solutions.
  • Example formulations were added to sorbitol or glycerol.
  • EP 1 683 417 A has octenidine formulations to the core comprising certain glycerol ethers.
  • Example formulations show glycerol or sodium gluconate as an additive.
  • US 4,420,484 relates to solutions of antimicrobial amino and ammonium compounds. Also shown is octenidine in a formulation with PEG.
  • WO 2007/023066 A relates to solutions of octenidine dihydrochloride for wound and mucous membrane disinfection, where it was an object to add additives, such as e.g. Replace phenoxyethanol with other alcohols. For example, it is proposed e.g. Add pentane-1,2-diol. Glycerol is mentioned as an additive.
  • the present invention relates to octenidine or a pharmaceutical salt thereof, in particular octidene dihydrochloride intended for co-therapeutic administration of the octenidine in solution with a polyhydric alcohol of formula 1: (HC-OH) a (HO-C-OH) b (HCH) c , where a, b, c are integers, where a + b is at least 2, preferably at least 3, c is selected from 0, 1 or a number from the range from 2 to a + b, additionally with one or more aldehyde groups if they form (cyclic) hemiacetals or acetals with one of the hydroxy groups and / or one or more keto groups optionally as acetal (or ketal) with one of the hydroxy groups, if appropriate additionally with one or more carboxylic acid groups
  • Polyalcohol is a cyclic hemiacetal or acetal, preferably with ring sizes of 5 to 7 atoms, or
  • the present invention relates to a pharmaceutical composition
  • a pharmaceutical composition comprising a solution of octenidine, preferably octenidine dihydrochloride, or one of its pharmaceutically acceptable salts and glucose with a glucose concentration of 0.01% to 12% (w / v), preferably 0.1 % to 10%, more preferably from 0.5% to 7.5%, most preferably from 2.5% to 5%, and an octenidine concentration of from 0.0001% to 5% (w / w), preferably from 0.001% to 1%, more preferably from 0.002% to 0.5%, optionally together with a carrier.
  • Octenidine is a highly effective bacteriostatic / bactericidal agent that is widely used in wound cleansing and preoperatively for disinfecting the surgical site, especially as a dihydrochloride salt. It has hitherto mostly been used as an aqueous solution in the concentration 0.1% (w / v) or as a dilution 1: 1 with NaCl physio . However, the excellent inhibition on prokaryotes also has certain disadvantages for the growth of eukaryotic cells, which, if properly wounded, must proliferate and differentiate to produce a well-adherent, tight wound closure. The stability of the cellular coverage is dependent on the formation of molecular interaction of the tissue matrix with cell surface molecules.
  • Octenidine is superficially antibacterial due to its affinity to bacterial surfaces.
  • octendidine has a disinfecting / antimicrobial action against fungi and viruses which can fully develop by administration with a polyalcohol according to the invention.
  • the polyalcohol also supports a wound healing-desired stabilization of the cell dressing, as can be seen from the cell adhesion test shown in the examples.
  • compositions of the invention show on the one hand the Efficacy in improving cell adhesion which has been demonstrated to be particularly preferred experimentally in the range of 1 g / L to 25 g / L (0.1% to 2.5%).
  • hypotonic octenisept involves an increased incidence of wound pain due to the mode of action of the receptors and ion channels involved in nociception. It is reduced by the application of the compositions of the invention for the proposed joint administration to wounds and sensitive mucous membranes with approximately isotonic solutions (equivalent to -5% glucose) or occasionally also some hypotonic solutions (corresponding to 2.5% glucose) the negative effect on the nociception or eliminated. This achieves freedom from pain and a substantial improvement in treatment, and in particular also a subsequent reaction in applications such as on the peritoneum, avoiding a fluid shift.
  • octenidine is provided together with a polyalcohol for co-administration.
  • This polyhydric alcohol preferably comprises a basic structure of formula 1: (HC-OH) a (HO-C-OH) b (HCH) c
  • a + b are at least 2, at least 3, at least 4, at least 5, at least 6 or even At least 7.
  • a is preferably 0, 1, 2, 3, 4, 5, 6 or at least 7.
  • b can be selected from 0, 1, 2, 3, 4, 5, 6 or at least 7.
  • the definitions of a and b specify the number of hydroxyl groups important according to the invention.
  • the polyalcohols have at least 4, preferably at least 5, 6, 7 or even at least 8 hydroxyl groups.
  • the basic structure of the above formula 1 is present as a polymer, in particular polycondensate, polyether or polyester.
  • larger structural elements of the formula 1 can also be present as such polymers, polycondensates, polyethers or polyesters, where a linking O or OC (O) of the polyether or polyester has not been given in the above formula and is possible as an additional linking structural element.
  • poly is to be understood as indicating the above structural elements, which may occur at least 2 times, preferably 3 times, more preferably 4 times, more preferably 5 times or even at least 6 times of polymers can be up to 5000, up to 4000, up to 3000, up to 2000, up to 1000, up to 800, up to 500 or up to 300 elements of formula 1 are provided.
  • the elements can be constructed uniformly or homogeneously from the same basic element, or heterogeneously from mixtures thereof. Heterogeneous are preferably carbohydrate polymers of sugar monomers or derivatives thereof.
  • the polyalcohols according to the invention may additionally be provided with one or more aldehyde groups, provided that they form (cyclic) hemiacetals or acetals with one of the hydroxy groups or one or more keto groups, optionally provided as acetal with a hydroxy group.
  • aldehydes as acetals is particularly preferred because aldehyde groups are potentially toxic due to their high reactivity. Specifically, therefore, the aldehyde is in equilibrium with its acetal, preferably at least 95%, more preferably at least 98%, even more preferably at least 99%, as the acetal in equilibrium with the open aldehyde structure at physiological conditions, especially at 37 ° C.
  • a keto group is provided, this is also in preferred embodiments, at least 95%, preferably at least 98%, at least 99% as acetal with one of the hydroxyl groups of the polyhydric alcohol (intramolecular) in equilibrium at physiological conditions, especially 37 0 C before.
  • the hemiacetals or acetals preferably form intramolecular rings with 5, 6, 7, 8 or even 9 atoms.
  • the polyalcohol, in particular in the form of an acetal, preferably comprises a glycoside.
  • the polyhydric alcohol of the basic structure of formula 1 may have a carboxylic acid group, provided that the polyhydric alcohol is a cyclic hemiacetal or acetal, preferably with ring sizes of 5-7 atoms.
  • acid groups are less effective together with octenidine, for example, was shown by the glucuronic that nevertheless increased efficacy was recorded (compared to conventional Octenisept ®).
  • Glucuronic acid is a carboxylic acid which is analogous to glucose as a 6-atom cyclic acetal, wherein the sixth carbon atom is oxidized to the carboxylic acid.
  • the present invention relates in a further aspect to a kit comprising a polyhydric alcohol as defined above and octenidine or pharmaceutical salts thereof, in particular octenidine dihydrochloride, preferably intended for common therapeutic administration in solution.
  • octenidine or its salt may be provided according to the kit as dissolved octenidine.
  • the polyalcohol can already be dissolved. Such a solution allows rapid use of octenidine, especially for disinfection.
  • the present invention relates to a pharmaceutical composition in the form of a solution comprising a polyhydric alcohol as defined above and octenidine or pharmaceutical salts thereof, in particular octenidine dihydrochloride. Also disclosed are mixtures of the polyalcohol with octenidine as a pharmaceutical composition. Solid mixtures may be provided in particular for later dissolution immediately prior to administration.
  • the polyhydric alcohol according to the present invention is a carbohydrate of the empirical formula 2: C n (H 2 O) 1n , where n is an integer of at least 3, preferably 4, 5, 6, 7, 8, 9, 10, 11 or at least 12 and m is an integer in the range of n-15% to n + 15% (rounded to integers), preferably n 1, n or n + 1.
  • the rounding is done mathematically, ie decimal places of., 5 are rounded up or., 4999 ... rounded off.
  • these carbohydrates can also be polymerized, in particular polycondensed, to soluble carbohydrate oligo- or polymeric. In particular, the ability to form solutions without clouding by the polyhydric alcohol is particularly preferred.
  • the preparation according to the present invention is in the form of a gel, in particular hydrogel
  • the polyalcohol according to the invention is not understood to be a gelling agent, especially since a gelling agent is not regarded as a soluble substance but as a solvated semi-solid structure.
  • the polyalcohol is uncharged.
  • weakly acidic polyalcohols such as glucuronic acid, are possible, the best results are obtained with uncharged polyalcohols.
  • the polyhydric alcohol is a weak acid, the pKa value of the polyhydric alcohol is preferably greater than 3, more preferably greater than 3.5, greater than 4, greater than 4.5 or greater than 5.
  • the polyhydric alcohol is a mono- or disaccharide or a deoxy or monocarbon acid derivative of a mono- or disaccharide.
  • the polyhydric alcohol comprises an aldose or ketose, preferably an aldohexose, aldopentose, ketohexose or a ketopentose.
  • polyalcohols according to the invention are glucose, galactose, fructose, fucose, maltose, ribose, deoxyribose, deoxyglucose, in particular 2-deoxyglucose, sucrose, lactose, glucuronic acid, dextrose, isomalt, maltitol syrup, polyglucose, glucans and fructooligosaccharides.
  • octenidine or the polyalcohol are dissolved in aqueous solutions, preferably pure water.
  • low levels of alcohol may be provided as a solvent, for example, ethanol, propanol or isobutanol.
  • the alcohol content is preferably less than 5%, less than 3%, less than 2% or less than 1%.
  • the polyalcohol is in solution for administration with octenidine at a concentration of at least 0.001%, at least 0.005% or at least 0.01%, preferably at least 0.025%, more preferably at least 0.1%, at least 0.5%, at least 1%, most preferably at least 2.5% (w / v), provided.
  • concentration (w / v) herein refers to a weight per volume concentration.
  • the maximum concentration of the polyhydric alcohol in solution for administration with octenidine is 12%, preferably 10%, especially to 7.5%, most preferably to 5% (w / v).
  • octenidine in solutions for administration with the polyalcohol or in the common solution of the composition or in the kit has an octenidine concentration of at least 0.0001%, particularly preferably at least 0.001%, particularly preferably at least 0.002%, at least 0.005%, at least 0.01% or at least 0.05% (w / w).
  • the octenidine concentration is up to 5%, up to 1%, up to 0.5% or up to 0.2% (w / w).
  • the polyhydric alcohol according to the present invention can prevent a masking effect of salt, in particular NaCl on octenidine
  • the salt concentration, in particular NaCl concentration a maximum of 0.5% (w / v), preferably not more than 0.1%, not more than 0.05%, not more than 0.01%, more preferably not more than 0.005% most preferably not more than 0.001%.
  • the polyhydric alcohol and / or octenidine is present in the preparation of dedicated octenidine of the kit or composition in a carrier.
  • the carrier is preferably selected from a gel, preferably a hydrogel or a wound dressing or swab, which is optionally impregnated with a solution containing the polyhydric alcohol and / or octenidine.
  • Further carriers comprise slow-release carriers which release the active ingredient combination as a longer-acting application with a time delay or slowed down. Such a preparation with a corresponding carrier is particularly suitable for topical and rapid application.
  • the octenidine, kit or composition according to the present invention with octenidine and the polyhydric alcohol for common therapeutic administration is particularly useful for treating wounds or burns, particularly the skin, mucous membrane, especially the vagina, abdominal cavity, internal organs surgical interventions or as prophylaxis before surgical interventions or for the treatment and prevention of infections, in particular wound infections, preferably infections of burn wounds, in particular the skin, a mucous membrane, in particular the vagina, the abdominal cavity, internal organs, in particular during surgical interventions or as prophylaxis Surgery, determined.
  • the present invention relates to the polyhydric alcohol, preferably glucose, intended to enhance the effect of octenidine in its therapeutic use; and octenidine or a pharmaceutical salt thereof, e.g. Octenidine dihydrochloride intended for co-therapeutic administration with the polyalcohol, preferably glucose.
  • polyhydric alcohol preferably glucose
  • octenidine or a pharmaceutical salt thereof e.g. Octenidine dihydrochloride intended for co-therapeutic administration with the polyalcohol, preferably glucose.
  • glucose 5% as an easy-to-handle, widely available and easily calculable diluent allows octenidine to bind with uninhibited affinity to the bacterial surfaces, as the bacteriostatic effect is fully present and, on the other hand, promotes wound healing-like stabilization of the cell dressing, such as cell adhesion tests is apparent.
  • the present invention relates to a kit comprising glucose and octenidine or a pharmaceutical salt thereof, in particular octenidine dihydrochloride.
  • the effect according to the invention of improved wound healing occurs in particular coadministration of this kit.
  • a kit can also be provided, in which glucose and octenidine are provided separately.
  • the ingredients may be for co-administration.
  • glucose or octenidine or both components is in solution.
  • the use of dissolved glucose or octenidine, particularly preferably both dissolved glucose and dissolved octenidine allows rapid application, for example by mixing the two substances or the two solutions and subsequent application.
  • the solution in which the kit or the pharmaceutical composition according to the present invention is provided is preferably an aqueous solution.
  • water may be provided as a pure solvent, but also with minor other organic solvents such as alcohols.
  • the alcohol content of such a solution is preferably below 10%, in particular below 5%, particularly preferably at most 2% or below 1%.
  • the polyhydric alcohol concentration, preferably glucose concentration, in a polyalcohol solution of the octenidine administration or in the pharmaceutical composition in which both substances are already mixed is preferably at least 0.001%, at least 0.005% or at least 0.01%, most preferably at least 0 , 05% or at least 0.1%, especially preferably at least 0.5%, at least 1% or at least 2.5% (all percentages w / v).
  • the polyalcohol concentration, preferably glucose concentration is a maximum of 30%, a maximum of 20%, a maximum of 10%, a maximum of 8%, a maximum of 5% (w / v).
  • the kit comprising a polyalcohol solution and an octenidine solution provided to the mixture, e.g.
  • the preferred concentrations are correspondingly increased, e.g. at a mixing ratio of 1: 1 double, e.g. for the polyalcohol solution, a polyalcohol concentration of 5-10% and for the octenidine solution the octenidine concentration of 0.004-1% is most preferred.
  • concentration (w / v) used herein refers to weight per volume of English weight per volume. Concentration (w / w) also used herein refers to weight per total weight of the particular preparation, preparation or solution.
  • the octenidine solution for co-administration with glucose or the pharmaceutical composition comprises Send a solution of octenidine, an octenidine concentration of at least 0.0001% (w / w), preferably of at least 0.001%, more preferably at least 0.002%, at least 0.005%, at least 0.01% or at least 0.05%.
  • maximum concentrations of octenidine are up to 10% (w / w), preferably to 5%, to 1%, more preferably to 0.5%, even more preferably to 0.2%.
  • a salt content especially a high NaCl concentration, e.g. in physiological conditions inhibit the effects of octenidine.
  • glucose can prevent this inhibiting effect, in particular embodiments of the present invention the NaCl concentration is limited.
  • the octenidine solution for administration with glucose or the pharmaceutical composition according to the invention comprises a salt concentration, in particular NaCl concentration of less than 0.1% (w / v), preferably less than 0.05% or less than 0.01%, more preferably less than 0.05%, most preferably less than 0.001%.
  • the carrier is a gel, especially a hydrogel.
  • a wound dressing or swab is a wound dressing or swab, optionally impregnated with a solution containing glucose and / or octenidine.
  • a wound dressing or gel can be administered directly or by addition of the other component selected from glucose and / or octenidine.
  • Other carriers include slow-release carriers, such as microencapsulations, which release the active ingredient combination as a longer-acting application with a time delay or slower release.
  • a gel or hydrogel can be made with conventional gel formers, for example, cellulose derivatives such as hydroxyethyl cellulose.
  • Other possible carrier media include emulsions, preferably oil in water or water in oil emulsions and liposomes.
  • the solutions according to the invention are particularly preferably provided as germ-free.
  • the present invention relates to a pharmaceutical composition in the form of a solution comprising glucose and octenidine, preferably as in the composition Octenisept ®.
  • the kit according to the invention or the composition is used in particular for the production of a medicament for the therapeutic see administration for the treatment of wounds or burns or for the treatment or prevention of infections, in particular wound infections.
  • the composition or the kit is preferably used for the treatment of wounds, infections, in particular wound infections, skin burns, a mucous membrane, in particular the vagina, internal organs, the abdominal cavity, in particular during surgical interventions.
  • the preparations according to the invention thus provide a particularly practical means which can be used effectively as a disinfectant in surgical interventions.
  • the pharmaceutical composition according to the invention or the glucose or octenidine solution of the kit are provided in particular at physiological pH.
  • the pH may thus be, for example, between 5 and 9, preferably up to pH 8.
  • the pH may be adjusted by suitable buffers such as organic acids such as citric acid, acetic acid, fumaric acid or malic acid and inorganic acids , As hydrochloric acid, phosphoric acid or sulfuric acid, or their alkali or alkaline earth metal salts, in particular sodium, potassium, magnesium and calcium, or by buffer of pharmaceutically acceptable bases, eg of NaOH.
  • the solution of octenidine or the entire pharmaceutical composition is a clear solution without precipitated octenidine.
  • this solution may be incorporated into the carrier material of the present invention, such as a gel or hydrogel or wound dressing.
  • Fig. 1 Inverse microscope picture precipitated Octenidinkristal- Ie from a Octenisept ® -NaCl solution
  • Fig. 2 modification of the Octenisept ® induced cell detachment by the addition of NaCl or glucose in the cell Detachment assay with crystal violet
  • a graphical bar representation of the results: bars represent the mean ⁇ standard deviation of four independent experiments
  • b Photograph of the cell lawn.
  • 3A and 3B Modification of Octenisept ® induced cell detachment by addition of various carbohydrates in the cell-Detachment assay using crystal violet.
  • Fig. 4 Konzentrationsabhfitikeit of glucose additives on the Octenisept ® induced cell detachment from the culture substrate in the crystal-violet assay. After washing and staining the adherent cells with crystal violet, the absorbance at 550 nm was measured. (Bars represent the mean ⁇ standard deviation of 3 readings). The dilution is carried out from a 0.1% octyl tenidinates (Octenisept ®) with a 5% glucose solution in proportions of 0, 1: 200 to 1: 2.
  • the ideal constellation for wound treatment is I. the superficial destruction of the microbial biofilm on the wound and II.
  • the anchoring of proliferating cells with the tissue scaffold corresponds in cell culture to the formation of stable connections between the cytoskeleton, integrins and the matrix at the bottom of the culture dishes.
  • the resistance to detachment of the cell lawn under mechanical stress such as washing is determined.
  • the remaining cell lawn is stained with crystal violet and quantified by photometric absorption measurement. Additional effects caused by the use of specific glucose solutions in defined dilutions with Octenisept ® that enhance cell adhesion and explain the observed improved wound healing, are shown.
  • Octenisept ® (Schulke & Mayr) solution (0.1% (w / w) Octenidindihydro- chloride and 2% (w / w) 2-phenoxyethanol in H 2 O); NaCl solution (0.9% (w / v) in H 2 O); 5% glucose (Mayrhofer Pharmazeutika) glucose solution 5% (w / v) in H 2 O;
  • Lactose, 2-deoxyglucose, sucrose, fructose, polyethylene glycol, chondroitin 4-sulphate, chondroitin 6-sulphate, dermatan sulphate and dextran sulphate were used in a final concentration of 5% (w / v) in H 2 O used sterile filtered.
  • the human glioblastoma cell line U373 were cultured in Dulbecco 's Mo- dified Eagle Medium (DMEM) supplemented with 10% PCS (Gibco TM), 2 mM Glutamine (PAA) and 100 U / ml penicillin / streptomycin (PAA) at 37 0 C and 5% CO 2 cultured.
  • DMEM Dulbecco 's Mo- dified Eagle Medium
  • PCS Gibco TM
  • PAA 2 mM Glutamine
  • PAA penicillin / streptomycin
  • Example 6 Effects of glucose and NaCl additives ® on the Octenisept induced cell detachment from the culture substrate in the crystal violet assay
  • Octenisept ® resulted in a significant reduction of cell adhesion, which has been improved by means of polar monomers such as glucose, 2-deoxyglucose, fructose, and glucuronic acid, as well as disaccharides such as lactose, sucrose, and polymers such as polyethylene glycol again.
  • polar monomers such as glucose, 2-deoxyglucose, fructose, and glucuronic acid
  • disaccharides such as lactose, sucrose
  • polymers such as polyethylene glycol again.
  • Charged polymers such as chondroitin-4-sulfate, chondroitin-6-sulfate, dermatan sulfate and dextran sulfate could not achieve this effect, reduced rather, the adhesion significantly lower than the values of NaCl.
  • Glucuronic acid as an inner ester is therefore positively effective, but not phosphate or sulfate derivatized carbohydrates, which additionally enhance the detachment of the cells by octenidine.
  • Example 8 Konzentrationsabhfitikeit of glucose additives on the Octenisept ® induced cell detachment from the culture substrate in the crystal-violet assay
  • Octenisept ® causes a considerable reduction in cell adherence, which was tended to be improved by the addition of glucose 1: 200 or 1: 100.
  • the optimum of the protective effect was determined at a dilution of 1:20 and show with increasing concentrations, strong fluctuations but no constant, significantly increased protective effect.

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PCT/EP2009/065111 2008-11-14 2009-11-13 Octenidin-zusammensetzung WO2010055122A1 (de)

Priority Applications (22)

Application Number Priority Date Filing Date Title
PL09756292T PL2291185T3 (pl) 2008-11-14 2009-11-13 Kompozycja oktenidyny
NZ59277509A NZ592775A (en) 2008-11-14 2009-11-13 Octenidine composition
BRPI0915269A BRPI0915269A2 (pt) 2008-11-14 2009-11-13 octonidina ou um sal farmacêutico do mesmo, kit farmacêutico, composição farmacêutica e agente farmacêutico
SI200930217T SI2291185T1 (sl) 2008-11-14 2009-11-13 Sestavek oktenidina
UAA201107410A UA108190C2 (xx) 2008-11-14 2009-11-13 Розчин, який містить октенідин
EP09756292A EP2291185B1 (de) 2008-11-14 2009-11-13 Octenidin-zusammensetzung
DK09756292T DK2291185T3 (da) 2008-11-14 2009-11-13 Octenidine composition
MX2011005092A MX2011005092A (es) 2008-11-14 2009-11-13 Composicion de octenidina.
US13/128,266 US8940324B2 (en) 2008-11-14 2009-11-13 Octenidine composition
ES09756292T ES2381815T3 (es) 2008-11-14 2009-11-13 Composición de octenidina
JP2011536025A JP5756018B2 (ja) 2008-11-14 2009-11-13 オクテニジン組成物
AU2009315654A AU2009315654B2 (en) 2008-11-14 2009-11-13 Octenidine composition
AT09756292T ATE538788T1 (de) 2008-11-14 2009-11-13 Octenidin-zusammensetzung
CA2742921A CA2742921A1 (en) 2008-11-14 2009-11-13 Octenidine composition
RSP20120133 RS52299B (en) 2008-11-14 2009-11-13 OCTENIDINE COMPOSITION
EA201100762A EA028177B1 (ru) 2008-11-14 2009-11-13 Состав, содержащий октенидин
CN2009801448968A CN102209542A (zh) 2008-11-14 2009-11-13 奥替尼啶组合物
ZA2011/03126A ZA201103126B (en) 2008-11-14 2011-04-28 Octenidine composition
IL212596A IL212596A (en) 2008-11-14 2011-05-01 Its octanidine or its pharmaceutical salt is combined in a solution with polyalcohol
HK11107685A HK1156838A1 (en) 2008-11-14 2011-07-25 Octenidine composition
HRP20120277AT HRP20120277T1 (hr) 2008-11-14 2012-03-28 Sastav oktenidina
US14/528,869 US20150126557A1 (en) 2008-11-14 2014-10-30 Octenidine composition

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EP08450183.2 2008-11-14

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KR101718306B1 (ko) 2015-07-27 2017-03-27 주식회사 퍼슨 옥테니딘염산염(Octenidine dihydrochloride)의 개선된 합성방법과 옥타니딘염산염을 포함하는 새로운 복합제의 제조방법
US20180263243A1 (en) * 2015-09-25 2018-09-20 Flechsig Patent Company Llc Novel plant protecting compositions and uses thereof
PL233480B1 (pl) * 2017-09-28 2019-10-31 Phytopharm Kleka Spolka Akcyjna Koncentrat na bazie soli bis[4-(RHN)-1-pirydynio]alkanów w formie hydrożelu oraz sposób jego otrzymywania
EP3771339A1 (en) * 2019-07-29 2021-02-03 The Procter & Gamble Company Disinfectant composition
CN113827565A (zh) * 2020-06-16 2021-12-24 深圳长久康联生物科技有限公司 一种抗感染喷剂敷料及其制备方法、应用
CN113082029B (zh) * 2021-03-02 2022-07-15 浙大宁波理工学院 一种伤口清洗消毒剂
CN117159784B (zh) * 2023-03-31 2024-04-19 鹏拓生物科技(杭州)有限公司 用于难愈性创面修复的液体创可贴及其制备方法和应用

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EP2443925A1 (en) * 2010-10-22 2012-04-25 L'Air Liquide Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Textile sheetlike structure impregnated with an antimicrobial active ingredient preparation and with a support material based on polyolefin

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CY1112730T1 (el) 2016-02-10
CN102209542A (zh) 2011-10-05
US20150126557A1 (en) 2015-05-07
SI2291185T1 (sl) 2012-06-29
UA108190C2 (xx) 2015-04-10
HRP20120277T1 (hr) 2012-05-31
RS52299B (en) 2012-12-31
AU2009315654A1 (en) 2010-05-20
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IL212596A (en) 2017-09-28
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ATE538788T1 (de) 2012-01-15
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